EP4378310A1 - Utilisation de l'hydroxythyrosol (ht) et de ses dérivés comme phytorégulateur - Google Patents
Utilisation de l'hydroxythyrosol (ht) et de ses dérivés comme phytorégulateur Download PDFInfo
- Publication number
- EP4378310A1 EP4378310A1 EP23212868.6A EP23212868A EP4378310A1 EP 4378310 A1 EP4378310 A1 EP 4378310A1 EP 23212868 A EP23212868 A EP 23212868A EP 4378310 A1 EP4378310 A1 EP 4378310A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- plant
- hydroxytyrosol
- ppm
- control
- extract
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 claims abstract description 173
- 235000003248 hydroxytyrosol Nutrition 0.000 claims abstract description 88
- 229940095066 hydroxytyrosol Drugs 0.000 claims abstract description 88
- 239000000284 extract Substances 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 19
- 230000000694 effects Effects 0.000 claims abstract description 13
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 Hydroxytyrosol Glycoside Chemical class 0.000 claims abstract description 10
- 229930182470 glycoside Natural products 0.000 claims abstract description 10
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims abstract description 10
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 claims abstract description 10
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000009472 formulation Methods 0.000 claims abstract description 7
- DBLDQZASZZMNSL-QMMMGPOBSA-N L-tyrosinol Natural products OC[C@@H](N)CC1=CC=C(O)C=C1 DBLDQZASZZMNSL-QMMMGPOBSA-N 0.000 claims abstract description 6
- 235000004330 tyrosol Nutrition 0.000 claims abstract description 6
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000012141 vanillin Nutrition 0.000 claims abstract description 5
- 239000002671 adjuvant Substances 0.000 claims description 12
- 230000012010 growth Effects 0.000 claims description 12
- 239000004009 herbicide Substances 0.000 claims description 12
- 238000011161 development Methods 0.000 claims description 8
- LPRNQMUKVDHCFX-RKQHYHRCSA-N Glucovanillin Chemical compound COC1=CC(C=O)=CC=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 LPRNQMUKVDHCFX-RKQHYHRCSA-N 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 49
- 230000035784 germination Effects 0.000 description 31
- 240000008042 Zea mays Species 0.000 description 30
- 238000011282 treatment Methods 0.000 description 27
- 239000000243 solution Substances 0.000 description 19
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 17
- 240000007817 Olea europaea Species 0.000 description 15
- 235000007244 Zea mays Nutrition 0.000 description 13
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 13
- 235000009973 maize Nutrition 0.000 description 13
- 238000012360 testing method Methods 0.000 description 11
- 241000033016 Lolium rigidum Species 0.000 description 10
- 240000003768 Solanum lycopersicum Species 0.000 description 10
- 230000008511 vegetative development Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 230000018109 developmental process Effects 0.000 description 7
- 230000001965 increasing effect Effects 0.000 description 7
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- 238000009825 accumulation Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000008635 plant growth Effects 0.000 description 5
- 150000008442 polyphenolic compounds Chemical class 0.000 description 5
- 235000013824 polyphenols Nutrition 0.000 description 5
- 239000003642 reactive oxygen metabolite Substances 0.000 description 5
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- 238000001727 in vivo Methods 0.000 description 4
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- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 description 3
- RFWGABANNQMHMZ-UHFFFAOYSA-N 8-acetoxy-7-acetyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline Natural products CC=C1C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O RFWGABANNQMHMZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HKVGJQVJNQRJPO-UHFFFAOYSA-N Demethyloleuropein Natural products O1C=C(C(O)=O)C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(=CC)C1OC1OC(CO)C(O)C(O)C1O HKVGJQVJNQRJPO-UHFFFAOYSA-N 0.000 description 3
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 description 3
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 description 3
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 description 3
- RFWGABANNQMHMZ-HYYSZPHDSA-N Oleuropein Chemical compound O([C@@H]1OC=C([C@H](C1=CC)CC(=O)OCCC=1C=C(O)C(O)=CC=1)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RFWGABANNQMHMZ-HYYSZPHDSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- MDZKJHQSJHYOHJ-UHFFFAOYSA-N crataegolic acid Natural products C1C(O)C(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MDZKJHQSJHYOHJ-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000002262 irrigation Effects 0.000 description 3
- 238000003973 irrigation Methods 0.000 description 3
- MDZKJHQSJHYOHJ-LLICELPBSA-N maslinic acid Chemical compound C1[C@@H](O)[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MDZKJHQSJHYOHJ-LLICELPBSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229940100243 oleanolic acid Drugs 0.000 description 3
- 235000011576 oleuropein Nutrition 0.000 description 3
- RFWGABANNQMHMZ-CARRXEGNSA-N oleuropein Natural products COC(=O)C1=CO[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)C(=CC)[C@H]1CC(=O)OCCc3ccc(O)c(O)c3 RFWGABANNQMHMZ-CARRXEGNSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 230000008121 plant development Effects 0.000 description 3
- 230000037039 plant physiology Effects 0.000 description 3
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 description 3
- HSTOKWSFWGCZMH-UHFFFAOYSA-N 3,3'-diaminobenzidine Chemical compound C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 HSTOKWSFWGCZMH-UHFFFAOYSA-N 0.000 description 2
- 208000005156 Dehydration Diseases 0.000 description 2
- CITFYDYEWQIEPX-UHFFFAOYSA-N Flavanol Natural products O1C2=CC(OCC=C(C)C)=CC(O)=C2C(=O)C(O)C1C1=CC=C(O)C=C1 CITFYDYEWQIEPX-UHFFFAOYSA-N 0.000 description 2
- 229930189936 Glyoxalase Natural products 0.000 description 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 2
- SXEHKFHPFVVDIR-UHFFFAOYSA-N [4-(4-hydrazinylphenyl)phenyl]hydrazine Chemical compound C1=CC(NN)=CC=C1C1=CC=C(NN)C=C1 SXEHKFHPFVVDIR-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
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- 235000019258 dehydroacetic acid Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 150000002206 flavan-3-ols Chemical class 0.000 description 2
- 235000011987 flavanols Nutrition 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 230000001744 histochemical effect Effects 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
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- 238000004519 manufacturing process Methods 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 230000002256 phytoregulatory effect Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
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- 230000001737 promoting effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
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- WVQBLGZPHOPPFO-LBPRGKRZSA-N (S)-metolachlor Chemical compound CCC1=CC=CC(C)=C1N([C@@H](C)COC)C(=O)CCl WVQBLGZPHOPPFO-LBPRGKRZSA-N 0.000 description 1
- PQQITYGQJLPDFC-UHFFFAOYSA-N 2-(3,4-dihydroxy)-phenyl-ethyl-beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCCC1=CC=C(O)C(O)=C1 PQQITYGQJLPDFC-UHFFFAOYSA-N 0.000 description 1
- PQQITYGQJLPDFC-RKQHYHRCSA-N 2-(3,4-dihydroxyphenyl)-ethyl-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OCCC1=CC=C(O)C(O)=C1 PQQITYGQJLPDFC-RKQHYHRCSA-N 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000221779 Fusarium sambucinum Species 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- 102000003820 Lipoxygenases Human genes 0.000 description 1
- 108090000128 Lipoxygenases Proteins 0.000 description 1
- 241000207836 Olea <angiosperm> Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 239000005617 S-Metolachlor Substances 0.000 description 1
- 235000002560 Solanum lycopersicum Nutrition 0.000 description 1
- 239000005621 Terbuthylazine Substances 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 230000036579 abiotic stress Effects 0.000 description 1
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- 229930003944 flavone Natural products 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- NWKFECICNXDNOQ-UHFFFAOYSA-N flavylium Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=[O+]1 NWKFECICNXDNOQ-UHFFFAOYSA-N 0.000 description 1
- 239000003324 growth hormone secretagogue Substances 0.000 description 1
- 230000015784 hyperosmotic salinity response Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 1
- 150000002515 isoflavone derivatives Chemical class 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
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- 230000003204 osmotic effect Effects 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
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- 230000019612 pigmentation Effects 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
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- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES202231026 | 2022-11-29 |
Publications (1)
Publication Number | Publication Date |
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EP4378310A1 true EP4378310A1 (fr) | 2024-06-05 |
Family
ID=89190458
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP23212868.6A Pending EP4378310A1 (fr) | 2022-11-29 | 2023-11-29 | Utilisation de l'hydroxythyrosol (ht) et de ses dérivés comme phytorégulateur |
Country Status (1)
Country | Link |
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EP (1) | EP4378310A1 (fr) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2408134A1 (es) | 2011-12-14 | 2013-06-18 | Consejo Superior De Investigaciones Científicas (Csic) | Procedimiento para la obtención de una solución favorecedora del crecimiento de plantas a partir de aguas de lavado del proceso de elaboración de aceitunas verdes estilo español y uso de dicha solución. |
EP3539383A1 (fr) * | 2016-11-03 | 2019-09-18 | Consejo Superior de Investigaciones Cientificas (CSIC) | Utilisation de 3,4-dihydroxy-phényl-glycol (dhfg) comme phytorégulateur |
-
2023
- 2023-11-29 EP EP23212868.6A patent/EP4378310A1/fr active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2408134A1 (es) | 2011-12-14 | 2013-06-18 | Consejo Superior De Investigaciones Científicas (Csic) | Procedimiento para la obtención de una solución favorecedora del crecimiento de plantas a partir de aguas de lavado del proceso de elaboración de aceitunas verdes estilo español y uso de dicha solución. |
ES2408134B1 (es) * | 2011-12-14 | 2014-04-15 | Consejo Superior De Investigaciones Científicas (Csic) | Procedimiento para la obtención de una solución favorecedora del crecimiento de plantas a partir de aguas de lavado del proceso de elaboración de aceitunas verdes estilo español y uso de dicha solución. |
EP3539383A1 (fr) * | 2016-11-03 | 2019-09-18 | Consejo Superior de Investigaciones Cientificas (CSIC) | Utilisation de 3,4-dihydroxy-phényl-glycol (dhfg) comme phytorégulateur |
Non-Patent Citations (10)
Title |
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"Olive Oil : Minor Constituents and Health", 25 July 2008, CRC PRESS, ISBN: 978-0-429-13690-0, article BOSKOU DIMITRIOS: "Phenolic Compounds in Olives and Olive Oil - Book Chapter", pages: 11 - 44, XP055801548, DOI: 10.1201/9781420059946.ch3 * |
EL-ABBASSI ABDELILAH ET AL: "Potential applications of olive mill wastewater as biopesticide for crops protection", SCIENCE OF THE TOTAL ENVIRONMENT, ELSEVIER, AMSTERDAM, NL, vol. 576, 22 October 2016 (2016-10-22), pages 10 - 21, XP029849932, ISSN: 0048-9697, DOI: 10.1016/J.SCITOTENV.2016.10.032 * |
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